Sodium Bicarbonate → 3-[(Phenylacetyl)amino]-2-azetidinone

HRID 2418195Notes

Reaction equation

HRID 2418195 reaction equation
ClC(Cl)(Cl)COC(NC([N:12]1[CH2:15][CH:14]([NH:16][C:17](=[O:25])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]1=[O:26])C(C)C)=O.C(=O)(O)[O-].[Na+]>C(O)(=O)C.[Zn]>[C:19]1([CH2:18][C:17]([NH:16][CH:14]2[CH2:15][NH:12][C:13]2=[O:26])=[O:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 536478601-[1-(2,2,2-Trichloroethoxycarbonylamino)-2-methylpropyl]-3-(2-phenylacetamido)-2-azetidinone

Product 1

HCID 132120483-[(Phenylacetyl)amino]-2-azetidinoneYield 58.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Conditions

Temperature
5 °C

Procedure

1-[1-(2,2,2-Trichloroethoxycarbonylamino)-2-methylpropyl]-3-(2-phenylacetamido)-2-azetidinone (1.13 g.) was dissolved in a 90% acetic acid aqueous solution (20 ml.), and the solution was cooled to 5° C. Zinc powder (1.62 g.) was added dropwise to said solution in 5 minutes, and the mixture was stirred for 30 minutes. Furthermore, zinc powder (1.62 g.) was added to said mixture, and the mixture was stirred for 2 days. The reaction mixture was neutralized with a sodium bicarbonate aqueous solution, and extracted with methylene chloride. The extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off from the solution. The residue (0.65 g.) was subjected to preparative thin layer chromatography using silica gel [developing solvent; a mixed solvent of ethyl acetate, ethyl methyl ketone, water and formic acid (volume ratio 5:3:1:1)], isolated and purified to give 3-(2-phenylacetamido)-2-azetidinone (0.3 g.). Mp 190° to 192° C.

Workup

  1. customin 5 minutes
  2. stirringthe mixture was stirred for 2 days
  3. extractionextracted with methylene chloride
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off from the solution
  7. customa mixed solvent of ethyl acetate, ethyl methyl ketone, water and formic acid (volume ratio 5:3:1:1)], isolated
  8. custompurified

Sources & evidence

ORD record
ord-f4bc437713974b899029cf7e2f22fd1c
Source dataset
uspto-grants-1984_09
Patent number
US04472300

Reaction notes

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